Tetrachlorvinphos

Last updated
Tetrachlorvinphos
(Z)-Tetrachlorvinphos structure.svg
Names
Preferred IUPAC name
(Z)-2-Chloro-1-(2,4,5-trichlorophenyl)ethen-1-yl dimethyl phosphate
Other names
Stirofos; CVMP; [1] TCVP [2]
Identifiers
3D model (JSmol)
1890909
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.040.772 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 244-865-4
KEGG
PubChem CID
RTECS number
  • TB9100000
UNII
UN number 2783
  • InChI=1S/C10H9Cl4O4P/c1-16-19(15,17-2)18-10(5-11)6-3-8(13)9(14)4-7(6)12/h3-5H,1-2H3/b10-5-
    Key: UBCKGWBNUIFUST-YHYXMXQVSA-N
  • COP(=O)(OC)O/C(=C\Cl)/c1cc(c(cc1Cl)Cl)Cl
Properties
C10H9Cl4O4P
Molar mass 365.95 g·mol−1
Melting point 97 to 98 °C (207 to 208 °F; 370 to 371 K) [3]
Pharmacology
QP53AF14 ( WHO ) QP53BB04 ( WHO )
Hazards
GHS labelling:
GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
Warning
H302, H332, H410
P261, P264, P270, P271, P273, P301+P312, P304+P312, P304+P340, P312, P330, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tetrachlorvinphos is an organophosphate insecticide used to kill fleas and ticks. [2]

Contents

History

Tetrachlorvinphos was initially registered for use in the United States in 1966 by the U.S. Department of Agriculture. Tetrachlorvinphos was originally registered for use on various food crops, livestock, pet animals, and in or around buildings. The crop uses were voluntarily canceled from product registrations in 1987. [4] In 2014, the Natural Resources Defense Council (NRDC) filed a lawsuit against the United States Environmental Protection Agency (EPA) seeking EPA to respond to NRDC's 2009 petition to ban tetrachlorvinphos in common pet flea treatment products. [5] [6]

Human health hazards

Symptoms of exposure to this material include increased perspiration, nausea, lachrymation, salivation, blurred vision, diarrhea, pulmonary edema, respiratory embarrassment and convulsions. The chemical material may be absorbed through the skin and is a lachrymator. It is a cholinesterase inhibitor and is a positive animal carcinogen. [7]

Chemical properties

The substance is insoluble in water. Flash point data are not available for this chemical; however, it is probably combustible. Tetrachlorvinphos is slowly hydrolyzed in neutral and aqueous acidic media. Is rapidly hydrolyzed in alkaline media. [7]

Alternative Chemical Names

This is a listing of alternate names for this chemical, including trade names and synonyms. [7]

Related Research Articles

<span class="mw-page-title-main">Ester</span> Compound derived from an acid

In chemistry, an ester is a compound derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.

<span class="mw-page-title-main">Corrosive substance</span> Substance that will damage or destroy other substances by means of a chemical reaction

A corrosive substance is one that will damage or destroy other substances with which it comes into contact by means of a chemical reaction.

<span class="mw-page-title-main">Permethrin</span> Medication and insecticide

Permethrin is a medication and an insecticide. As a medication, it is used to treat scabies and lice. It is applied to the skin as a cream or lotion. As an insecticide, it can be sprayed onto outer clothing or mosquito nets to kill the insects that touch them.

<span class="mw-page-title-main">Chlorfenvinphos</span> Chemical compound

Chlorfenvinphos is the common name of an organophosphorus compound that was widely used as an insecticide and an acaricide. The molecule itself can be described as an enol ester derived from dichloroacetophenone and diethylphosphonic acid. Chlorfenvinphos has been included in many products since its first use in 1963. However, because of its toxic effect as a cholinesterase inhibitor it has been banned in several countries, including the United States and the European Union. Its use in the United States was cancelled in 1991.

<span class="mw-page-title-main">Benzyl alcohol</span> Aromatic alcohol

Benzyl alcohol (also known as α-Cresol) is an aromatic alcohol with the formula C6H5CH2OH. The benzyl group is often abbreviated "Bn" (not to be confused with "Bz" which is used for benzoyl), thus benzyl alcohol is denoted as BnOH. Benzyl alcohol is a colorless liquid with a mild pleasant aromatic odor. It is a useful as a solvent for its polarity, low toxicity, and low vapor pressure. Benzyl alcohol has moderate solubility in water (4 g/100 mL) and is miscible in alcohols and diethyl ether. The anion produced by deprotonation of the alcohol group is known as benzylate or benzyloxide.

<span class="mw-page-title-main">Organophosphate</span> Organic compounds with the structure O=P(OR)3

In organic chemistry, organophosphates are a class of organophosphorus compounds with the general structure O=P(OR)3, a central phosphate molecule with alkyl or aromatic substituents. They can be considered as esters of phosphoric acid.

<span class="mw-page-title-main">Diazinon</span> Chemical compound

Diazinon, a colorless to dark brown liquid, is a thiophosphoric acid ester developed in 1952 by Ciba-Geigy, a Swiss chemical company. It is a nonsystemic organophosphate insecticide formerly used to control cockroaches, silverfish, ants, and fleas in residential, non-food buildings. Diazinon was heavily used during the 1970s and early 1980s for general-purpose gardening use and indoor pest control. A bait form was used to control scavenger wasps in the western U.S. Diazinon is used in flea collars for domestic pets in Australia and New Zealand. Residential uses of diazinon were outlawed in the U.S. in 2004 because of human health risks but it is still approved for agricultural uses. An emergency antidote is atropine.

Demeton-S-methyl is an organic compound with the molecular formula C6H15O3PS2. It was used as an organothiophosphate acaricide and organothiophosphate insecticide. It is flammable. With prolonged storage, Demeton-S-methyl becomes more toxic due to formation of a sulfonium derivative which has greater affinity to the human form of the acetylcholinesterase enzyme, and this may present a hazard in agricultural use.

<span class="mw-page-title-main">Phosphoric acids and phosphates</span>

A phosphoric acid, in the general sense, is a phosphorus oxoacid in which each phosphorus (P) atom is in the oxidation state +5, and is bonded to four oxygen (O) atoms, one of them through a double bond, arranged as the corners of a tetrahedron. Two or more of these PO
4
tetrahedra may be connected by shared single-bonded oxygens, forming linear or branched chains, cycles, or more complex structures. The single-bonded oxygen atoms that are not shared are completed with acidic hydrogen atoms. The general formula of a phosphoric acid is H
n+2−2x
P
n
O
3n+1−x
, where n is the number of phosphorus atoms and x is the number of fundamental cycles in the molecule's structure, between 0 and (n+2)/2.

Alkyl phosphates belong to a group of organic compounds called organophosphates. They are esters of phosphoric acid H3PO4 and corresponding alcohol. For example, the formula of methyl phosphate is CH3-H2PO4, dimethyl phosphate – (CH3)2HPO4 and trimethyl phosphate – (CH3)3PO4. Alkyl phosphates are widely distributed in nature, and form the basis of most biological processes. For example, high energy metabolites such as ATP and PEP are alkyl phosphates, as are nucleic acids such as DNA and RNA. Alkyl phosphates are also important medicinally, for example the HIV drug AZT is inactive until it becomes an alkyl phosphate in vivo.

<span class="mw-page-title-main">Phosphoryl chloride</span> Chemical compound

Phosphoryl chloride is a colourless liquid with the formula POCl3. Also known as Trichloro-Hydroxyphosphanium,it is 1.8±0.1 g/cm3 in density. It hydrolyses in moist air releasing phosphoric acid and fumes of hydrogen chloride. It is manufactured industrially on a large scale from phosphorus trichloride and oxygen or phosphorus pentoxide. It is mainly used to make phosphate esters such as tricresyl phosphate.

<span class="mw-page-title-main">Triethyl phosphate</span> Chemical compound

Triethyl phosphate is an organic chemical compound with the formula (C2H5)3PO4 or OP(OEt)3. It is a colorless liquid. It is the triester of ethanol and phosphoric acid and can be called "phosphoric acid, triethyl ester".

An esterase is a hydrolase enzyme that splits esters into an acid and an alcohol in a chemical reaction with water called hydrolysis.

This is the list of extremely hazardous substances defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act. The list can be found as an appendix to 40 C.F.R. 355. Updates as of 2006 can be seen on the Federal Register, 71 FR 47121.

<span class="mw-page-title-main">Dimethyl carbonate</span> Chemical compound

Dimethyl carbonate (DMC) is an organic compound with the formula OC(OCH3)2. It is a colourless, flammable liquid. It is classified as a carbonate ester. This compound has found use as a methylating agent and more recently as a solvent that is exempt from the restrictions placed on most volatile organic compounds (VOCs) in the United States. Dimethyl carbonate is often considered to be a green reagent.

<span class="mw-page-title-main">Lysol</span> Cleaning products brand name

Lysol is a brand of American cleaning and disinfecting products distributed by Reckitt, which markets the similar Dettol or Sagrotan in other markets. The line includes liquid solutions for hard and soft surfaces, air treatment, and hand washing. The active ingredient in many Lysol products is benzalkonium chloride, but the active ingredient in the Lysol "Power and Free" line is hydrogen peroxide. Lysol has been used since its invention in the late 19th century as a household and industrial cleaning agent, and previously as a medical disinfectant.

<span class="mw-page-title-main">Cyhalothrin</span> Synthetic pyrethroid used as insecticide

Cyhalothrin is the ISO common name for an organic compound that, in specific isomeric forms, is used as a pesticide. It is a pyrethroid, a class of synthetic insecticides that mimic the structure and properties of the naturally occurring insecticide pyrethrin which is present in the flowers of Chrysanthemum cinerariifolium. Pyrethroids such as cyhalothrin are often preferred as an active ingredient in agricultural insecticides because they are more cost-effective and longer acting than natural pyrethrins. λ-and γ-cyhalothrin are now used to control insects and spider mites in crops including cotton, cereals, potatoes and vegetables.

<span class="mw-page-title-main">Phosphamidon</span> Chemical compound

Phosphamidon is an organophosphate insecticide first reported in 1960. It acts as a cholinesterase inhibitor.

<span class="mw-page-title-main">Tefluthrin</span> Synthetic pyrethroid used as insecticide

Tefluthrin is the ISO common name for an organic compound that is used as a pesticide. It is a pyrethroid, a class of synthetic insecticides that mimic the structure and properties of the naturally occurring insecticide pyrethrin which is present in the flowers of Chrysanthemum cinerariifolium. Pyrethroids such as tefluthrin are often preferred as active ingredients in agricultural insecticides because they are more cost-effective and longer acting than natural pyrethrins. It is effective against soil pests because it can move as a vapour without irreversibly binding to soil particles: in this respect it differs from most other pyrethroids.

References

  1. Tetrachlorvinphos, alanwood.net
  2. 1 2 "Tetrachlorvinphos (TCVP)". Natural Resources Defense Council.
  3. "Tetrachlorvinphos". Sigma-Aldrich.
  4. "Archived copy" (PDF). Archived from the original (PDF) on 2014-08-09. Retrieved 2013-07-28.{{cite web}}: CS1 maint: archived copy as title (link)
  5. "EPA Sued Over Toxic Pesticides in Pet Flea Collars | EcoWatch". ecowatch.com. Archived from the original on 2014-02-09.
  6. "NRDC Sues EPA to Ban Two Toxic Pesticides in Pet Flea Collars".
  7. 1 2 3 "TETRACHLORVINPHOS | CAMEO Chemicals | NOAA".

This article contains public domain text from the EPA and the NOAA.